


The Predicament

by HazelDomain



Category: Supernatural
Genre: Angel Healing, Bad BDSM Etiquette, Bondage, M/M, Object Insertion, Predicament Bondage, Sex Toys, Size Kink, Soulless Sam Winchester, Suspension
Language: English
Status: Completed
Published: 2020-09-11
Updated: 2020-09-11
Packaged: 2021-03-06 14:14:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,202
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26400217
Author URL: https://archiveofourown.org/users/HazelDomain/pseuds/HazelDomain
Summary: “I’m guessing your arms will give out before your legs, but you sometimes surprise me,” Sam says. His fingers trail over Dean’s taut body, pausing to scratch at the peak of one nipple.“Unless I get out of the ropes,” Dean quips, and Sam laughs.“You won’t,” he says. “You’re going to stretch that hungry little hole of yours until you can’t take it any more, and when you cry uncle, I’ll let you down and fuck you.”In which Sam plans to have Dean take an absolutely massive tapered dildo, but isn't as good at bondage safety as he probably should have been.
Relationships: Castiel & Dean Winchester, Dean Winchester/Sam Winchester
Comments: 14
Kudos: 167
Collections: Supernatural Kink Meme





	The Predicament

“I have something different planned for tonight,” Sam says, and Dean shivers. There’s been an edge to Sam’s voice ever since he lost his soul. It’s dangerous, and Dean can’t deny that does something to him. 

“Yeah?” Dean asks, and Sam hums. He takes one of Dean’s hands, fastening something to the leather cuff already buckled tight. Dean cna’t see beyond the blindfold, but from the sound, it’s a chain. 

“You’ve been getting lazy,” Sam says, and Dean scowls. 

“Bullshit. That last hunt? I took down  _ six _ ghouls, you and all your early-morning cardio only managed to take down  _ two. _ ” 

“You know that’s not what I mean,” Sam says, fastening a chain to Dean’s other wrist cuff. “I mean during sex. You spread your legs and beg me, but in the end, I’m the one doing all the work.” 

“You want me to play cowboy for you?” Dean asks. He almost says  _ Sammy _ , but bites his tongue just in time. 

“I’ve got a better idea. A little exercise for you.” Sam’s moved back, and now the chains are tightening, drawing Dean’s arms up and apart. They pull just enough that his shoulders begin to hurt, and then there’s the sound of something wooden sliding along the floor. “Step up.”

Dean does, standing uncertainly on a wooden stool- no, two of them, he realizes. One for each foot, keeping his stance shoulder-width apart. Something presses against this hand and he takes it. 

“You’re going to open yourself up for me,” Sam says, and it doesn’t immediately make sense. Dean carefully turns the object around in his hand, trying to figure it out without dropping it. It’s hard, some kind of plastic, a circle about an inch in diameter… and another circle… 

It’s a dildo, Dean realizes. Bulbs in a line, each one getting bigger and bigger until-

“It’s a little big,” Dean says weakly.

“Not at first,” Sam says, and Dean can tell he’s smiling. He can imagine that hungry, wicked smile of his brother’s and he can feel himself getting hard as Sam takes the toy back. Fingers trail down the inside of Dean’s thigh, and something scrapes against the floor. 

“There’s a stand,” Sam provides helpfully, and that at least answers one of Dean’s questions. “And you’re going to lower yourself down onto it.”

There’s the sound of something wet as Sam strokes the toy, spreading lube over it’s surface. Without warning his attention turns upwards, one slick finger pushing into Dean without warning. Dean hisses, barely able to feel it before Sam retreats, leaving nothing but a wet feeling in his hole. A moment later, Sam pushes at one of the stools, forcing Dean to spread his legs wider. The smallest bulb of the toy is now pressing uncomfortably against the furrow of his ass, and Dean bites his lip. His cock is bobbing against his stomach. He can imagine Sam sitting there, silent and endlessly patient, watching Dean fuck himself open on this toy. 

Sam has so much patience now, at least when it comes to sex. Dean can easily imagine him sitting there, motionless, not even touching his own cock, watching Dean fruitlessly trying to fuck himself to orgasm. It won’t work, will just leave him sore and harder than ever, but what’s his alternative? 

“Ready?” Sam asks, and before Dean can say ‘for what’ the chain clanks, pulling Dean’s arms higher and further apart, and now he takes hold of the chains, testing the weight. The wrist cuffs are thick leather, with enough padding that they could take Dean’s full weight without bruising. It’s not the cuffs he’s worried about- it’s the  _ stretch.  _ He stands on his toes, trying to take some of the weight off. 

“I’m guessing your arms will give out before your legs, but you sometimes surprise me,” Sam says. His fingers trail over Dean’s taut body, pausing to scratch at the peak of one nipple. 

“Unless I get out of the ropes,” Dean quips, and Sam laughs. 

“You won’t,” he says. “You’re going to stretch that hungry little hole of yours until you can’t take it any more, and when you cry uncle, I’ll let you down and fuck you.” 

Dean’s a little put out- Sam’s good at restraints, but Dean’s good at getting loose. It’s saved his life more than once. 

“I’ll make you a bet,” he says, and Sam chuckles, low and rich enough that Dean leans down, just a bit, letting the tip of the toy catch against his hole. “I bet I’m out of this in twenty minutes. No interfering. And if I am… I get to fuck you.” 

Without warning, his hand is closing over Dean’s cock, his fingers still slick with the lube he used on the toy. He strokes, slow and maddening, the pad of his thumb rubbing against Dean’s frenulum. Dean shivers. 

“And what do I get, if you aren’t? We both know you’re already taking my cock when this is over.”

“What do you want?” 

There’s silence for a second, while Sam considers it. 

“I get to leave you up there,” he says finally. “Until I’ve seen enough.” 

Dean swallows. He’s pretty sure he can take the first three bulbs, probably even the first four- but it felt like there were at least seven, and the bottom one was way bigger than he was comfortable with. He wasn’t sure he  _ could _ take all of it. 

But Sam wouldn’t let him hurt himself. Struggle, and whine, and beg, and be uncomfortable, sure, but he wouldn’t let Dean really  _ injure _ himself. Probably. Definitely. If it came to that. 

“I’ll get out,” Dean said confidently. Sam hummed. 

“If I were you, I’d focus on getting that toy inside you. You can’t sit down unless it’s completely inside you, and the longer you try to avoid it, the faster you’re going to have to take it.” 

“No interfering,” Dean starts to say, but Sam is sliding a gag between his lips. Dean sucks at it, trying to get it wet and settled. It’s shaped like a cock, because Sam likes that, but it’s not deep enough to gag him. Just deep enough to keep his mouth full and his jaw open. 

‘ _ Because I know you love the feeling,’  _ Sam had said the first time he’d used it, and Dean hadn’t even had the dignity to protest. 

For a moment, he lets himself hang, taking stock of his predicament. With his arms stretched as far as they’ll go, he’s able to put his feet flat on the stools, taking the building pressure off his calves; but it won’t last. His shoulders are too tight, he can’t force his chest to expand further, he can’t breathe. Reluctantly, he stands back up on his toes, gasping air past the gag. 

Sam doesn’t make a sound, and Dean can imagine him there. Waiting, silently, watching his contraption torture Dean by inches while he does nothing. 

_ Let’s see how he likes this,  _ Dean thinks, and takes hold of the chains. Holding them tight, he steps off his wooden supports. If he hadn’t been holding tight, the force of his weight pulling taut would have dislocated his shoulders. But he’s planned for that and instead, the chains jerk against whatever it was Sam had used to secure them. 

They don’t pull free, which means that Sam is better than about 80% of the monsters Dean had escaped in his life. 

He steps back up onto the stools, palms hot and tingling from holding him up even that long. He tests the give of the restraints- there’s no slack. 

And then, just out of curiosity, he turns his attention to the toy. It’s well-secured, if nothing else. He can feel it pressing up between his cheeks, nudging at his hole, and it’s got even less give than the chains. 

He rocks against it a little, feeling it catching on his rim, and then he lowers himself over the first bulb. He can feel himself expanding around it, then tightening again, immediately trapping it inside him. 

Sam doesn’t react, and Dean’s face turns red. He has no idea where Sam is, where he’s watching from. He could be sprawled out in a chair, lazily stroking himself… or he could be only a few inches away, watching Dean’s face as he struggled. 

Dean lets himself sink down over the next section as he ponders it, shivering at the thought of what he looks like, and what it’s doing to Sam. The second one is easy, and he’s still plenty wet- exhaling slowly, Dean eases himself down over the third bulb. This one stretches a bit in the middle, making him moan, and once it’s inside, Dean feels pleasantly full. His rim is stretched with each motion, caught in the furrow between two bulbs. 

More importantly, though, is that his heel can touch one stool now, if he keeps the other one raised. 

He tries to swallow around the gag, almost sucking at it as he turns his attention to his hands. If he could just reach the buckles of the cuffs… Maybe...

Not even close. 

Which makes Sam smarter than 99% of the monsters who have tied Dean up, but he’s still got eighteen minutes before it’s time to panic. 

He settles back down, standing on both tiptoes and testing at the size of the next bulb. This one seems much bigger, and he has to pause a quarter of the way down to breathe, slowly, easing himself down. He can’t quite do it yet. 

There’s one last play in his book. If he can shift all his weight onto one foot, he could be able to reach to the side. He’ll only have a moment before he needs to fix his balance, but it will give him an idea of what the chains are anchored to. If he’s lucky, there’ll be something he can unhook. 

Breathing deep, he stretches his toes out, putting all his weight onto the left and leaping for the chain with his hand. The toy pulls at his rim as he rises slightly. 

It’s way too long, and there’s not nearly enough slack on the other side. He’s barely able to reach five inches up the length of the chain before he’s forced to give up. His foot returns to the right stool, his weight momentarily balanced-

And then it overturns, and he’s standing on nothing. 

He drops instantly, the next bulb forcing its way into him like a slippery ember. He screams and grabs at the chains, holding tight to keep him from falling further. Almost immediately, his arms begin to tremble. 

The next bulb is so big it almost seems like he could sit on it, but it’s wet and smooth and as Dean tests his weight on it, he can feel it forcing itself inside his sore hole. 

He screams again, trying to get Sam’s name out around the gag. 

His right leg swings, trying to find something to take his weight. He can feel the tips of the overturned stool legs, but they’re too small to do him any good. The stool on the left is too far away- trying to stand on it gives him only a moment of respite before the inside of his thigh begins to cramp. 

“ _ Sam! _ ” he tries again, but it’s no use. Apparently his brother considers their wager over, and is determined to see this out. “ _ Sam, I can’t _ -” 

He slips another inch, the toy that seemed large in his hand now seems massive. Maybe, if he had more time, but-

When climbing ropes he can use his legs, lock the rope around his calf or his forearm, but here, there’s nothing but the strength of his hands. He has until they give out, and the tendons in his wrists are already screaming. Sweat is rising all over his naked body, and he can imagine it running down his back, helping to lubricate the toy that’s about to ruin him. His palms are wet, and he can feel his grip slipping. 

His left hand cramps and he lets go on the chain, and it’s like time slows down. The last three bulbs push into him one millimeter at a time, spreading him wider and then relenting before returning, worse than before. He’s screaming by the time the first one is inside, and he doesn’t stop until his feet hit the ground. 

It’s fully embedded in his hole, and all Dean can do is gasp for breath. Something wet is trailing down his thigh. He doesn’t know whether it’s sweat or blood, and he’s afraid to look. If he moves a single muscle, complete agony is going to come rushing in. 

He can feel the tip of the toy pressing against his stomach from the inside, and it’s so huge he’s half convinced it’s protruding from his belly. Just under the breastbone, by the feel of it. 

But it’s not the sharp pain that comes from torn skin and bleeding muscle- it’s the dull, pounding ache of something blunt, pressing and cutting off circulation somewhere deep inside. 

“Sam,” he whimpers, because there’s something very wrong with Sam, but at the moment, there’s something very wrong with Dean, too. “Help.”

It feels like eons before he hears Sam approaching, the sound of something crashing to the ground as Sam exclaims “ _ oh shit. _ ” 

Arms wrap around him and he screams again as Sam tries to lift him off the toy. He shakes his head vehemently, desperate to keep the widest part of the largest bulb inside him. He can’t stretch around it, not again. 

Sam’s hands are on his face, removing the blindfold, removing the gag. 

“Help,” Dean whimpers, once his mouth is empty. 

“Yeah, I’m on it,” Sam responds, fumbling at the cuffs still holding Dean’s arms aloft. “Sorry, I went to get a drink. Stay hydrated and all that.” 

Dean can smell whiskey, somewhere behind Sam, the bottle lays shattered where he dropped it. 

“Hold onto my shoulders,” Sam commands, and Dean obeys without question, wrapping his arms around Sam’s neck. Sam adjusts something and the toy comes loose from it’s stand. Dean tries, for just a moment, to hold his own weight, and then Sam is lowering him to the ground. 

“Lay back. Just… lay down. That’s right,” Sam says. The concrete is cold against Dean’s back, sweat turning clammy as he shivers. He’s afraid to move… anything. Cramps ripple through his belly, and there’s a burning pain in his ass any time he moves. 

“God, look at you,” Sam is saying. “Spread your legs, let me see.” 

Dean does, feeling the massive toy shifting inside him as he spreads his thighs as wide as he can. 

“You took the whole thing,” Sam says, and there’s something like awe in his voice. His fingers trail around the flared base, tickling at Dean’s skin in a way he can feel even despite everything else. “I didn’t think you could.” 

“I can’t,” Dean whines. He needs Sam to pull it out, but he’s terrified of what will happen when he tries. “It’s too big.” 

“Do you want it out?”

Dean nods, burying his face in his shoulder. He’s too humiliated and in too much pain to deal with the way Sam is staring at him. 

“Relax,” Sam says, and there’s a gentle pressure that turns into agony as his rim is stretched again. Dean arches, hands clawing at Sam’s wrists. 

“Stop, stop stop stop,” he gasps, too nervous to ask about tearing, about whether he’s bleeding out on the floor. Tears are leaking out of the corners of his eyes. 

“We might have to involve an actual doctor for this, Dean,” Sam says doubtfully. “If it hurts that bad when I barely even touch it.” 

“I’d rather die here on the floor than try to drive all the way into town like this,” Dean answers, throwing his arm over his face and collapsing back onto the concrete. 

“... Cas?”

“Would he even fix something like this?” 

“Why wouldn’t he?” 

“I dunno, something about angels being unable to heal sodomy wounds inflicted by blood siblings?” 

“Technically, I didn’t do this,” Sam points out, and Dean gives him the finger without looking. 

“I can try calling him,” Dean says after a moment. 

“I already did.” 

“Yeah, but like…” 

There’s a whole mess of undiscussed topics there, and they aren’t gonna broach them now. Dean shoots off a mental SOS and tries to decide which outcome he’d hate less. 

Sam’s back to gently probing Dean’s hole, fingers circling the entrance. 

“I can see all the way inside you,” he says, a little breathlessly. 

“What?”

“It’s clear,” Sam says, pushing gently against the base in a way that makes Dean hiss. “The toy’s clear. The way it’s holding you open… fuck, Dean, I can see you getting tight around it. I can see when you go tense and I just…” His hand slips up over Dean’s perineum, cupping his balls before giving his cock a perfunctory stroke. “I could come just looking at you like this.” 

“That makes one of us,” Dean groans. He considers closing his legs, trying to push Sam away, but the way his brother’s staring at him… it’s like Sam’s never seen him before. 

“Can I take a picture?” Sam asks, and Dean’s breath catches because once again, there’s something  _ wrong _ with his brother. But… Dean’s never been able to tell him no. 

That’s how Cas finds them, about six minutes later. Sam’s palming himself through his sweatpants, taking pictures on his phone while Dean holds his junk out of the way and tries not to audibly sob when the toy shifts. 

“You…. needed my assistance?” Cas says hesitantly. 

“We need you to smite something,” Dean says, reaching for a joke and falling flat. “Something inside me.” 

Castiel stands up a little straighter at that. 

“Of course,” he says. He takes three steps and crouches down, pressing his fingertips to Dean’s forehead without even a cursory investigation of the wound. Instantly, the pressure is gone as the toy vanishes. A moment later the burning in his hole and the throbbing in his belly is gone too, replaced by the vaguely-warm  _ neutral _ that Dean’s come to associate with an angel rebuilding. 

“Was…. there anything else?” Cas asks, after Dean’s spent about a full minute breathing in relief. 

“Not unless you want to have a cigarette,” Sam answers. Castiel looks confused, but his eyes don’t leave Dean’s face. Dean keeps his forearm over his eyes, and pretends not to notice. 

“I’m good. Thanks, Cas. I owe you a huge one. Seriously. Name it.” 

Castiel looks like he’s going to say something, but changes his mind at the last second. 

“I assume this is another one of the things we don’t talk about,” he says instead, and Dean nods. “Very well.” 

He’s gone before either of them can respond, and for a second Dean feels bad, like he should have offered the guy a beer or something. 

He’ll do it next time, when they can all pretend this never happened. 

“Goddamn angel glow fucked up the video,” Sam says, looking at his phone. 

Dean reaches for his pants. 

  
  
  
  


**Author's Note:**

> Sam's BDSM etiquette apparently stayed in hell with his soul.


End file.
